Urea → (S)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@H:5]([CH:7]([C:11]([OH:13])=O)[C:8]([OH:10])=O)[CH3:6])[CH3:2].[NH2:15][C:16]([NH2:18])=[O:17]>C(OC(=O)C)(=O)C>[O:17]=[C:16]1[NH:18][C:8](=[O:10])[CH:7]([C@H:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:14])[C:11](=[O:13])[NH:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of (S)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid (5 g, 25 mmol) and urea (1.8 g, 29.4 mmol) in acetic anhydride (15 mL) was placed in a microwave reactor and allowed to react under microwave irradiation at 60° C. for 30 minutes. After cooled to room temperature, the mixture was quenched by sodium bicarbonate and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by silica gel chromatography to afford the product (S)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoate (2.85 g, yield 50%).